Don't Date the Boss's Son!

By Dr. Robert Wallace

November 26, 2019 5 min read

DR. WALLACE: I graduated from high school this past June and was fortunate enough to find a pretty good full-time job. I work in the office as a typist and receptionist, and I enjoy my work, plus I receive a really good salary for a girl just out of high school.

My boss has a son who is working in the office part time as a mail boy about twice a week. He is very outgoing, and we always talk for a few minutes. He is a big flirt, and I enjoy the attention he gives me.

Since I am sort of attracted to him, I was wondering if I should become a bit assertive and tell him that I'd like to go out with him. I'm 18, and he had his 16th birthday last week. Do you see anything wrong with me dating a 16-year-old? — Office Girl, San Francisco

OFFICE GIRL: To directly answer your question, I would keep the relationship with the boss's son as is; do not suggest a date with him. You enjoy your job, you've graduated from high school, and this young man has two years left in high school.

But most of all, he is your employer's son! It's not a good idea to mix your social life with this good, well-paying job. By all means, be polite and friendly to this young man, but don't suggest anything further.


DR. WALLACE: I'm 16, and my mom doesn't approve of the guys I go out with. I don't know what to do to get her to change her mind. About three months ago, I was dating a hot guy, but we broke up. My mom told me that she never knew what I saw in this boy. She thought he was immature, but he actually wasn't. He was pretty cool and nice, but after a few months, it became apparent that we didn't have a lot in common and our personalities didn't quite fit together. We broke up amiably, and I still call this boy a good friend. After all, he is a nice, respectable guy; we just weren't a perfect fit. Then I started dating a new young man, but my mom didn't like that because boy No. 2 was my ex's best friend! Then, after I stopped dating boy No. 2, I started seeing a third guy who was interested in me, who happens to also be a good friend of boy No. 2. Also, No. 3 does not know No. 1; he's just a casual friend of No. 2. I hope you are keeping up with all the details of my story!

This really upset my mom. She said that it sounded to her like I was being passed around and I'd go out with any guy who asked me on a date. This isn't true! I really like this third guy, and he likes me. He's a very sweet guy and a good friend. I am a virgin, so I'm not being passed around. Mom won't allow me to go out any more with this third boy and refuses to allow me to drive over to his house (he lives on the other side of our town). He and I have a great connection, far stronger and better than either of the first two nice guys.

I love my mother very much, and I know that she loves me, but when it comes to boyfriends, we don't see eye-to-eye. What's the best way to get my mom to let me see my new boyfriend? Please help me, if you can; I really feel this latest boy is a keeper! — Happy Now With No. 3, Portland, Oregon

HAPPY NOW: You might be surprised to hear that I receive many letters similar to yours. I do encourage teens to platonically date several potential matches, both for the experience and to learn how different personalities interact with yours. This will be very important for you to draw from later in your life when you consider marriage. For now, here's my standard advice: Have your current boyfriend call your mother and introduce himself. Have him tell Mom he thinks you are a super girl, and he enjoys your company. Have him finish by asking if he could stop by the house and meet your mother face-to-face. It would be difficult for a mom to say no to this if he is polite and earnest on the telephone. The better your mom gets to know your current boyfriend, the better she will be able to learn about his character and the more comfortable she will be with him. As for you, do share with your mother that you are not sexually active — and you plan to keep it that way.

Dr. Robert Wallace welcomes questions from readers. Although he is unable to reply to all of them individually, he will answer as many as possible in this column. Email him at [email protected] To find out more about Dr. Robert Wallace and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at

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